Escape to Island Paradise

Your Home Away from Home!

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Oceanside Islamorada

Immerse yourself in the luxury and beauty of Oceanside Resort, a brand-new gated community with 9 beachfront homes nestled in the heart of Islamorada.

Each 4 bedroom home invites you to experience modern coastal comfort while its nearly 3,000 square feet of indoor space provide ample room for family and friends. Every stylishly furnished bedroom comes complete with an en suite bathroom, and an expansive living/dining area opens directly onto a private patio & pool. Plus, savor delicious food prepared fresh from your own fully equipped kitchen or take advantage of numerous nearby restaurants, such as Morada Bay and Square Grouper, where breathtaking views meet tantalizing cuisine. Our resort, at mile marker 82, is just minutes away!

Each luxurious Oceanside home offers parking for two vehicles, a private pool, kitchen with all stainless steel appliances, large capacity washer and dryer, high-speed internet, smart TVs in every bedroom, and much more!

Weekly & Monthly Rates Available

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Seaside Sanctuary
(House 2)

8 guests • 4 bedrooms • 4.5 bathrooms

Experience the serenity of a blissful oasis where natural beauty harmoniously blends with modern comforts. Step into this opulent home that exudes an aura of tranquility, inviting you to unwind and rejuvenate amidst its peaceful ambiance.

Book House 2

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Tropical Haven (House 3)

8 guests • 4 bedrooms • 4.5 bathrooms

Indulge in the enchanting hues of the sand and sea as you step into this sublimely decorated home, evoking the essence of a captivating tropical island escape. Allow yourself to be transported to a paradise of comfort and relaxation, where every detail has been carefully curated to create a truly immersive and unforgettable experience.

Book House 3

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Coastal Retreat (House 4)

8 guests • 4 bedrooms • 4.5 bathrooms

Embodying the very essence of coastal charm, this captivating contemporary home stands as the quintessential gathering place for both family and friends. With its allure and modern design, this abode creates an inviting atmosphere that fosters shared moments and cherished connections.

Book House 4

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What People Are Saying

Memorable family vacation
“Staying at a beautiful property, where all your needs are easily met, always makes for a sweet vacation. This home is the ideal place due to its location, the comfortable layout of the interior space, and because of the lovely outdoor pool and living areas. The host, Giovanna, is incredibly helpful and very responsive. The home is well stocked and extremely clean. We will be back!”

— Jeremy R., House 4 guest
(03/2024)

“Amazing home & great location, in the heart of Upper Matecumbe. walking distance to a dozen + places for dinner, a mile to the grouper. The place is spotless and very tastefully done. Giovanna was extremely responsive and helpful for anything we asked. Looking forward to our next trip to the Keys. Thanks for everything.”

— Luke, House 2 guest
(03/2024)

Eat, Drink, Play and Explore

Indulge in the best Islamorada has to offer with local’s favorite restaurants and breweries. Spend the morning paddle boarding on the water and discover the native wildlife. Visit attractions and dive into the history of Islamorada.

Discover Islamorada